2,6-Lutidine → HCID 86738872, compound

HRID 851387Notes

Reaction equation

HRID 851387 reaction equation
[CH:1]([NH:3][C@H:4]1[C:7](=[O:8])[NH:6][C@@H:5]1[CH2:9][C:10]([O:16][CH3:17])=[CH:11][C:12]([O:14][CH3:15])=[O:13])=O.N1C(C)=CC=CC=1C.P(Cl)(Cl)(Cl)=O>ClCCl.C(OCC)(=O)C>[N+:3]([C@H:4]1[C:7](=[O:8])[NH:6][C@@H:5]1[CH2:9][C:10]([O:16][CH3:17])=[CH:11][C:12]([O:14][CH3:15])=[O:13])#[C-:1]

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 24813Phosphorus oxychlorideHCID 86738871HCID 86738871, compound

Product 1

HCID 86738872HCID 86738872, compoundYield 56.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 4-[(2R,3R)-3-formamido-4-oxoazetidin-2-yl]-3-methoxybut-2-enoate [(E,Z)-isomeric mixture] (133 mg) and 2,6lutidine (0.96 ml) in dichloromethane (3 ml) was added phosphorus oxychloride (0.15 ml) at 0°. After stirring at the same temperature for four hours, the reaction mixture was diluted with ethyl acetate (20 ml), and washed with a dilute aqueous sodium chloride, dilute phosphoric acid, a dilute aqueous sodium chloride, ice-water, and a saturated aqueous solution of sodium chloride in turn. Drying over magnesium sulfate and removal of the solvent gave a brown oil, which was chromatographed on silica gel (2 g) eluting with 3% methanol in dichloromethane to give methyl 4-[(2R,3R)-3-isocyano-4-oxoazetidin-2-yl]-3-methoxybut-2-enoate [(E,Z)-isomeric mixture] (70 mg) as a crystalline solid

Workup

  1. washwashed with a dilute aqueous sodium chloride, dilute phosphoric acid
  2. dry with materialDrying over magnesium sulfate and removal of the solvent
  3. customgave a brown oil, which
  4. customwas chromatographed on silica gel (2 g)
  5. washeluting with 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-d31654eabb7c479587d783682bc6dc2f
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Reaction notes

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